Annapolis is dotted with small stages — bars, restaurants and coffee shops — where late-night entertainment features singer-songwriters full of hope, middle school teachers keeping their love of music alive and regional groups always looking for another good place to play.
These are venues to explore in January and February, Annapolis’ quiet months. I’ve put together a list that’s not comprehensive, and most small venues post their lineups on Facebook or Instagram.
Take a little time, do a little research and you might discover something new.
Stan & Joe’s Saloon: The cozy, wood-paneled bar on West Street has music six nights a week, including one of Annapolis’ longest-running open-mic nights on Mondays and karaoke on Wednesdays. Russ & Friends takes the stage at 9:45 p.m. Friday, followed by Honey Sol at 9:45 p.m. Saturday and Mixed Business at 9 p.m. Sunday.
49 West: This coffee shop and art bar has music six to seven nights a week, usually in its 40-seat back room. Guest bands mix into the schedule of regulars such as Dave Chappell, the Unified Jazz Ensemble, the Songbird Collective, Dan Haas, Skribe and others. Saturday features singer-songwriter Brody Kean at 7 p.m. and the duo Blank Page at 8:30.
Annapolis Smokehouse and Tavern: The barbecue restaurant on Bay Ridge Road features music every Friday night. This week, Loop of Boom opens at 8 p.m. for Steve Cyphers, former frontman for Blue Miracle, and his new group.
Market House: The historic market at City Dock has been experimenting with music a few nights a week, posting the band lineup on its Facebook page. At 8:30 p.m. Friday, it’s Kings of Marigold.
Middleton Tavern: Located in a historic building, this restaurant has been a mainstay downtown since the 1970s. There’s live music every weekend, a mix of bands downstairs and a piano bar upstairs. At 10 p.m. Friday, the cover band Noelle and Jeff are on tap in the bar.
Dark Horse Tavern: This tavern on Bay Ridge Avenue posts its acts daily on its Facebook and Instagram pages. The shows are usually at 9 p.m. on Wednesdays through Saturdays and 6 p.m. Sundays. This Saturday, it’s The Slugs.
Here are more great things to do in Annapolis.
Twelfth Night concert
7 p.m. Saturday
And you thought the holidays were over. The Hammond Harwood House celebrates Christmas like the Colonials with its annual Twelfth Night concert. The Empressa Ensemble will perform La Fête des Rois, music and readings honoring the Marquis de Lafayette’s bicentennial celebration.
Lafayette returned to the United States in 1824, visiting Annapolis in December. He probably missed the Twelfth Night celebrations, which Included figures like the King of Mischief and Queen of Competence. Tickets are $75, or $65 for members of the historic building.
Lectures digging up the past
2-3 p.m. Saturday
Jim Gibb, director of environmental archaeology at the Smithsonian Environmental Research Center in Edgewater, will kick off the monthly lecture series “Histories Revealed” at the Woodlawn History Center — a visitor center and museum — highlighting archaeological research on the road to the American Revolution.
The center is housed in a home that dates to 1735, where tobacco planter William Sellman, his family and the enslaved people who worked their plantation would have experienced this month’s topic: “Maryland on the Eve of the Seven Years’ War.” Admission is free, but registration is requested.
Artisan Fair closing day
10 a.m. to 4 p.m. Sunday
It’s the final day of the Artisan Fair at Quiet Waters Park. Area crafting and art guilds have had their work on display and for sale since November. Here’s a chance to see what’s left. Admission to the park by car is $6.
Ricky Scaggs bluegrass concert
7:30 p.m. Sunday
With 15 Grammys, multi-instrument virtuoso Ricky Skaggs is a master of country music. He returns to Annapolis for the third time since 2016, bringing his band Kentucky Thunder to Maryland Hall for a Rams Head Presents concert.
Skaggs has been one of country music’s best-known voices since the early 1980s with hits like “Highway 40 Blues,” “Country Boy” and “Heartbroke.” Now 70, he is focused on the mandolin and bluegrass, touring nationally with his all-acoustic group of young musicians.
Tickets are $55-$100.
Bingo on the circle
7:30-9 p.m. Tuesday
Head to Reynold’s Tavern on Church Circle for weekly musical bingo in the 1747 Pub, located in the basement. Sing along as the host offers clues to songs you thought you knew.
They’re back
8:30 a.m. to 5 p.m. Wednesday
It’s not much of an event unless you’re going to one of the legislative receptions, but the General Assembly returns for its 90-day session on Wednesday.
The session is a lively time to tour the State House. Lawmakers are in session most weekdays, and you can sometimes catch a senator or delegate on the run. But lunch tables will be harder to get, and it’s no one’s favorite time to go looking for a parking spot downtown.
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